Addition polymerizable polymeric compounds

Abstract

Addition polymerizable polymeric compounds produced by esterification reaction or addition reaction of a copolymer having pendent carboxyl groups and about 0.03 to 1.0 equivalent, based upon the carboxyl groups of said copolymer, of an ethylenically unsaturated compound having one oxirane ring, said copolymer being obtained by copolymerizing (1) about 10 to 95 percent by weight of at least one member selected from the group consisting of styrene and the methyl-substituted styrene derivatives (2) about 5 to 70 percent by weight of at least one ethylenically unsaturated mono- or di-carboxylic acid, its anhydride or its monoalkyl of 1 to 4 carbon atoms ester, (3) up to about 30 percent weight of at least one member selected from the group consisting of acrylonitrile and methacrylonitrile, (4) up to about 85 percent by weight of at least one compound of the formula ##EQU1## wherein R 1 represents a hydrogen atom or methyl group; and R 2 represents an alkyl group having 1 to 12 carbon atoms, and (5) up to about 50 percent by weight, based upon the total weight of said compound (3) and/or (4), of at least one vinyl ester of a saturated aliphatic mono-carboxylic acid having 2 to 10 carbon atoms, and photopolymerizable compositions comprising (A) about 100 parts by weight of the above-described addition polymerizable polymeric compound, (B) about 5 to 70 parts by weight of at least one ethylenically unsaturated compound and (C) about 0.0001 to 10 parts by weight of a photopolymerization initiator. The compositions give photopolymerizable elements which are useful for various pattern or image yielding purposes and especially useful in making reliefs, particularly lithographic plates having an excellent printing durability.

What is claimed is: 
     
       1. In addition polymerizable polymeric compound obtained by esterification reaction of a copolymer having pendent carboxyl groups with about 0.10 to 0.8 equivalent, based upon the carboxyl groups of said copolymer, of an ethylenically unsaturated compound having one oxirane ring, said copolymer being obtained by copolymerizing (1) about 10 to 95 percent by weight of at least one member selected from the group consisting of styrene and the methyl-substituted styrene derivatives, (2) about 5 to 70 percent by weight of at least one ethylenically unsaturated compound selected from the group consisting of a monocarboxylic acid, a dicarboxylic acid, a dicarboxylic acid anhydride and a monoalkyl ester of a dicarboxylic acid wherein the alkyl group contains from 1 to 4 carbon atoms, (3) up to about 30 percent weight of at least one member selected from the group consisting of acrylonitrile and methacrylonitrile, (4) up to about 85 percent by weight of at least one compound of the formula ##EQU8## wherein R 1  represents a hydrogen atom or methyl group; and R 2  represents an alkyl group having 1 to 12 carbon atoms, and (5) up to about 50 percent by weight, based upon the total weight of said compound (3) and/or (4), of at least one vinyl ester of a saturated aliphatic nono-carboxylic acid having 2 to 10 carbon atoms. 
     
     
       2. An addition polymerizable polymeric compound as claimed in claim 1 wherein said ethylenically unsaturated compound having one oxirane ring comprises one compound selected from the group consisting of glycidyl acrylate, glycidyl methacrylate, glycidyl alpha-ethyl acrylate and allylglycidyl ether. 
     
     
       3. An addition polymerizable polymeric compound as claimed in claim 3 wherein said ethylenically unsaturated compound having one oxirane ring is glycidyl methacrylate. 
     
     
       4. An addition polymerizable polymeric compound as claimed in claim 3 wherein said ethylenically unsaturated compound having one oxirane ring is glycidyl acrylate. 
     
     
       5. An addition polymerizable polymeric compound as claimed in claim 1 wherein said copolymer is selected from the group consisting of styrene / acrylic acid copolymer, sytrene / acrylic acid / acrylonitrile copolymer, styrene / acrylic acid / acrylonitrile / n-butyl acrylate copolymer, styrene / methacrylic acid copolymer, styrene / acrylic acid / n-butyl acrylate copolymer, styrene / acrylic acid / methacrylonitrile copolymer, sytrene / acrylic acid / n-butyl acrylate / vinyl acetate copolymer, styrene / methacrylic acid / acrylonitrile / ethyl acrylate copolymer, styrene / acrylic acid / acrylonitrile / ethyl acrylate copolymer, styrene / acrylic acid / acrylonitrile / methacrylonitrile copolymer, styrene / acrylic acid / acrylonitrile / n-butyl acrylate / methyl acrylate copolymer, styrene / acrylic acid / acrylonitrile / n-octyl acrylate copolymer, styrene / acrylic acid / methyl methacrylate / n-butyl acrylate copolymer, alpha-methyl styrene / acrylic acid copolymer, vinyl toluene / acrylic acid / acrylonitrile copolymer, styrene / itaconic acid / n-butyl acrylate copolymer, styrene / monoethyl maleate / acrylonitrile / n-butyl acrylate copolymer, styrene / methacrylic acid / acrylonitrile / lauryl acrylate copolymer, styrene / acrylic acid / acrylonitrile / methacrylonitrile copolymer, styrene / methacrylic acid / n-butyl acrylate copolymer, styrene / methacrylic acid / methacrylonitrile / ethyl acrylate copolymer, styrene / methacrylic acid / acrylonitrile copolymer, styrene / acrylic acid / acrylonitrile / 2-ethylhexyl acrylate copolymer and styrene / methacrylic acid / acrylonitrile / 2-ethylhexyl acrylate. 
     
     
       6. An addition polymerizable polymeric compound as claimed in claim 5 wherein said polymer is a styrene / acrylic acid copolymer. 
     
     
       7. An addition polymerizable polymeric compound as claimed in claim 5 wherein said copolymer is a styrene / acrylic acid / acrylonitrile copolymer. 
     
     
       8. An addition polymerizable polymeric compound as claimed in claim 5 wherein said copolymer is a styrene / acrylic acid / acrylonitrile / n-butyl acrylate copolymer.